The Truth About Bobby
by CUIntheair
Summary: Bobby has a secret, he thought he'd never have to tell. When it comes out, he finds he doesn't know the half of it. Castiel has a secret of his own. Now let's watch them all deal with the aftermath.
1. Chapter 1 Angel From My Nightmare

Chapter 1- Hello there, Angel From My Nightmare

Jackie was walking with her toddler home from the neighbor's house. The day was warm and bright, the little boy rambled on happily in nonsense words, and the young mother smiled at the goodness of life. She smiled until she turned the corner to see her home a few yards away. Her expression changed immediately at the sight of a stranger, standing stock-still in her front yard. A stranger that was all too familiar. She knelt by her son and whispered desperately in his ear, "quick hunny, Mommy left her purse at the neighbor's. Can you be a big help and run go get it for me?" The child eagerly accepted the task and took off. Jackie stood back up only to see the stranger a few feet in front of her now, staring her down with a gaze that could cut glass. She had seen him only once before, and the memory of it still haunted her dreams. Here he stood before her once more, unchanged by the years. This was the man that had torn her from her family as a child. This was the man that had left her without a home, in what seemed an impossible place. This was the monster that had brought her through time, and abandoned her there. Her first thought was, "Not again!" Her next was, "I'm not a little girl any more, and I'll be damned..." Even within her own mind she knew she stood no chance. She stepped back and asked, "Why are you here? Please, I have a son." The man just looked at her with his intense, blue eyes. Was that curiosity, or maybe even sadness on his face? He spoke only two words, in a low, solemn voice, "I'm Sorry." And with that he placed a hand on her forehead and they were gone.

Maybe it was the strain of time-travel, or the emotional horror that Jackie was in, but she passed out upon (for lack of a better word) landing. When she came to, there was a warm blanket over her, and the smell of old paper and stale alcohol around her. She laid very quiet, pretending to still be asleep, listening. She could hear a man's voice. He was in the room, talking on the phone urgently. Talking about her. "I don't know why Dean, he just showed up with her and said he'd be back soon. She's unconscious for now, but you need to see this. I don't know where Cass found her, but... you need to get here now." At about this point, Jackie realized that it had happened again, her life was taken from her again by the man in the trench coat. What had happened to her family? She jumped up in a panic, and made a dash for what she guessed was the exit but the man in the room turned out to be faster than her. She swung at him, kicked him, all the while yelling for him to let her go. He seemed almost amused at her efforts. He held her wrists down and kindly mentioned handcuffs or rope. At about this time, Jackie heard a wonderfully familiar voice. She turned towards it, tears of relief welling in her eyes so she couldn't see. She ran towards him, and wrapped her arms around him, breathing his name aloud in her relief,

"Michael, thank God you're here." At this the body stiffened, and that familiar voice took on an unfamiliar tone,

"Not Michael yet, lady." Jackie pulled back, looking up at the man blinking the tears from her blue eyes. His comment had made her even more confused. She studied his face closely, and pulled back sharply.

"Who are you?" She asked looking into a face that was so close, and yet not the same. Into eyes eerily familiar.

"Who are _you?_" the man asked, "And why did Cass bring you here?" She stood up very straight and said,

"My name is Jackylyn Winchester, and if _Cass_ is the beast in the trench coat then I swear he needs to bring me home or I **will** kill him." The man that looked like Michael made a face like he'd been slapped and responded,

"Winchester?" Then the first man in the room, the tall one, walked over with Jackie's I.D., he pointed to the date on it. They spoke hurriedly for a moment, as soon as they seemed to decide on a course of action, however, the door opens again and an old man in a trucker cap walks in. When he saw Jackie, he froze, dropping the dusty books he had been holding. He stared for a moment at Jackie, then he quietly said,

"It's not... possible."


	2. Chapter 2 Back to the Future

Chapter II- Back to the Future

The room was still for barely a moment before Bobby Singer had grabbed an iron rod from an umbrella stand beside the door, and swung it towards Jackie. She tried diving out of the way, but the old hunter still managed a solid hit. Far from dissipating, the very much alive young woman fell to the ground, bringing the rod with her. She got back on her feet and brandished the weapon like a baseball bat. Bobby stepped back with a look of confused terror. The Winchester boys backed up, seeming simply confused. Jackie looked like a cornered animal, desperate and unwilling to go down without a fight. "That's iron." Bobby said, his hands held up as if Jackie was a cop.

"Yea, and it hurts when you hit someone with it, you horrible old man!" Not her most biting comeback but it seemed to strike a nerve in Bobby. "Now someone here is going to give me some answers or I swear I will break everything in this house, starting with bones." She held the rough metal rod a little higher to back her words up. Despite the threat, Bobby replied with,

"Why are you...How are you... here?" The angry expression on her face seemed to increase, but her response was cut short by Dean.

"What's going on here, people. Seriously. Bobby do you know her?" Jackie continued to look around for an escape, but was just as eager for answers. She chimed in sarcastically,

"Yea Bobby, do you _know_ me?" Her voice was full of contempt. Contempt for the situation, for the fear, for the pain in her side caused by the iron rod, and most especially for the damned devil in the trench coat. Bobby looked at her for a moment, he looked at her now-wrinkled pale green dress and little heels, her dark hair falling out of her pony-tail in wild curls, and he nodded.

"Yes, Ms. Jackie I think I do." Jackylyn's grip on the rod loosened for a fraction of a second, but then she stepped towards him aggressively,

" How do you know me? and where the hell am I?" For the first time during this encounter, Bobby looked more sad than confused,

"Well, I helped go through town putting up missing person posters with your name. I was on the search party through the woods. You were... my babysitter." Dean snorted, but Jackie just looked at him intensely, studying his face for the first time. She held the iron bar down by her side and stepped forward.

"Bobby. Bobby Singer?" He nodded, her face fell into sadness, and Sam and Dean exchanged confused looks. Jackie dropped the rod and began to tear up, "But you just turned 10. I was at your birthday party." Sam raised his hand as if he were in school,

"So, you guys know each other, and your last name is Winchester?" Jackylyn's attention immediately fell to the boys. She looked at Bobby and pointed towards Dean,

"Is this...?" But Bobby shook his head. Jackie's hand fell and she despairingly asked what year it was.

"2010" Dean replied. It looked as if she was ready to faint,

"fifty-two years." Her voice was a whisper.

Bobby looked at Sam and Dean, "Boys, meet your Grandmother."


	3. Chapter 3 Another Winchester

Chapter Three- Another Winchester

There was a heavy silence in the room as Sam and Dean processed this information. Somehow another relative had fallen through the cracks of their lives, the two boys who put family before anything else. Bobby had said grandmother, her last name was Winchester. She was petite and feminine and the thought of her holding a shotgun was ridiculous, so how could she be John Winchester's mother? And yet... her hair came down in dark waves and her eyes shone light blue. Her eyes were what convinced Dean, more than Bobby or the liscense. Her eyes reminded him of his own, but hers were far bluer. It took him just a moment to realize that Jackie had the exact same eyes as Adam. The shock of seeing those innocent blue eyes again hurt worse than he would have thought. Dean promised himself that he wouldn't see those eyes clouded in death this time, too late to be helped. This time he would teach and protect rather than shield his family from this life.

"So where are we?" Jackie asked calmly. Sam stepped forward, looking at her intensely. After a moment he responded to the question,

"South Dakota." Jackie folded her arms, closed her eyes and took a deep breath.

"I woke up this morning in Indiana in 1958." Another deep breath. "Bobby," She turned toward him with an expression of pity on her face. He looked so _old _it nearly horrified her. "Bobby, where is my husband?" Bobby looked at his shoes, like a child does when telling the teacher he forgot his homework. He took off his hat, and raised his head back toward her. The look said everything. "Bobby, where is Michael." Her voice took on a desperate edge, but with another deep breath she seemed to steel herself. "What about Johnny? You said these are his boys? Where is my son?" Bobby twisted his hat in his hands. "Miss Jackie, he's... well he's gone." Her body started to shake, but only for a moment. Dean's belief in her skyrocketed. She really was starting to remind him of John. He had been the only other person Dean had met that could take this much horrible news and process it through with so much practicality. He knew she would cry herself to sleep, but for now she needed information and was going to get it. She then turned her full attention to Sam and Dean. Her blue eyes taking in every detail.

"You look exactly like your grandfather Michael." Jackie's voice fell flat. Her eyes seemed to bore into Dean's very soul. "your hair is darker though, Michael had light brown hair. But Johnny had dark hair like me. At least he did..." Her voice cracked, she shook her head, then stepped forward, right in front of Sam. She had to crane her neck back to see his face. "Goodness, but you're tall. That certainly didn't come from me. Sit down, let me see your face." Sam complied silently, looking at her intensely, eyes wide. Sitting down, he was still tall enough that their eyes were nearly level. She was a little thing. She turned to Dean and Bobby and asked them both to sit as well. "I need to really see my grandsons. I obviously missed a lot. And Bobby I want to see that little boy I know somewhere under that hat and grey hair." When she looked, she really looked. She seemed to pick up on all the sadness or happiness that they had ever felt. Though none of them knew why, they felt like she was watching their memories, getting to know them. It was similar to the look that Sam gave Dean when he knew what he was thinking, but hers was at a deeper level. Every aspect of their faces, their calloused hands, scarred arms, felt exposed to her gaze. She studied Bobby the longest, finally sighing, seeming satisfied. "Well I've dealt with about as much as I think I can handle at this point. I think I will lie down for a little while, later we can figure more out. Is there a room I can go to, or do you want me to leave?" Her eyes drifted back to Dean when she asked this question. "Of course you can stay here." Bobby answered her, but she didn't hear him. Her eyes were trained on the person that had just entered the room. Entered without opening a door, with nothing more than a light rustle of wings. Jackie moved with a speed that belied the little heels and dress. She picked up the almost forgotten iron rod and hurled it at the angel. He stopped it without much effort, "Well I can see that she has awakened."

Authors note: this story is set sometime during the beginning of season five. Before Castiel has lost many powers.


	4. Chapter 4 Drifter

Chapter IV- Drifter

"You MONSTER! You JACKass!" Her words hit him in time with her bony little fists. He still held the iron rod to his side while she screeched at him, hair swinging, heels stamping, fists pounding against his chest. Bobby had never heard such an array of swear words from his old babysitter before. Sam and Dean looked at each other with shocked and slightly amused faces. She was clearly not doing any damage, but Castiel didn't stop her, allowing the force of her onslaught to wear her out. He looked down at her, piercing eyes overflowing with remorse. She simply continued her rant, "You Hell-bound, sorry waste of space, EVIL... _MONSTER!_" She spit out the last word with particular venom. His face, his inhuman gaze, the calm in his voice as he wrecked her existence, all of these had haunted her since childhood. He was the devil in the dark of her past, and when she had finally found some good in her life again, finally had a family, he had ripped her away once more. She swung at him one last time, and nearly collapsed into tears. Castiel reached for her, attempting to help her sit down, but she wrenched away violently, and slapped his face with a resounding crack.

The silence vibrated the air expectantly, interrupted only by Jackie's battered, sobbing breaths. She had backed away, fists at her sides. Her mastery of composure had dissipated upon sight of her personal nightmare. Castiel could hear her silent prayers for protection from what she thought of as a demon. He sighed, it was odd to be thought of in such a way. "I suppose it would be... prudent to tell you all of my second mission in this vessel. Though it had been planned long before, it lacked the immediate necessity of retrieving Dean from Hell."

"Yea, I'd say this deserves an explanation." Dean crossed his arms in front of him, looking at his friend rather sternly, before glancing back to Jackie. It either took a lot of nerve or some pretty strong backstory to slap an angel in the face. Sam walked forward, helping Jackie over to the couch, speaking to her quietly, trying to calm her. Her tears still came, but she never took her eyes off the angel.

"What are you? Why did you... why?" She fought for the right words. Sam and Dean didn't know where to look, at Castiel's sadness, this strange woman's torment, or Bobby's shell-shocked stare.

"It was... regrettable," the angel searched for the words, "my orders prohibited any explanation at the time. I spoke to you before," Castiel looked at Dean, "of the need for certain bloodlines coming together. Well, Michael Winchester was of the highest level of importance," His endless eyes turned sadly to Jackie, "and the bloodline needed, the only one strong enough, had been lost. We needed to wait until it resurfaced. The genetics are very," He closed his eyes in thought, "complex. It wasn't until just a few years ago that we were able to find a suitable match. Jackylyn Owens." The two pairs of eyes met, an intensity radiating through the air, "You were needed... we left you with your parents for as long as possible, but once Lillith began breaking the seals, we feared she would find you. We sent you to the correct time, to grow up with Michael, to marry him. All so that John Winchester could be born," He looked to Sam and Dean, "so that _you_ could be born."

"I was eight years old, you bastard." Jackie's voice had lost it's bite, she was glad to be hearing answers, even if she hadn't understood half of it. "Eight years old, and suddenly an orphan. Everyone thought I was crazy, I didn't understand how it had happened. No one had any clue what I was talking about, they were too busy with the war. You threw me back to 1942. After awhile, I thought I really was crazy. Maybe I was making things up, to block out some horrible memories or something. That's what my foster parents told me. That's what four different foster mothers told me. After the forth set gave up on me I stopped talking about it." Her eyes fell to the floor, then rose defiantly at Castiel, "You said 'orders', who the hell told you to ruin a little girl's life?"

"Heaven. I am an angel of the Lord." He let her process that information.

"Why should I believe that? And... even if it's true, if Heaven wanted me there, why would you pull me back here?" Everyone in the room was staring at Castiel, this was sure to be an interesting answer.


End file.
